TY - JOUR
T1 - Preparation and evaluation of a chiral stationary phase covalently bound with a chiral pseudo-18-crown-6 ether having a phenolic hydroxy group for enantiomer separation of amino compounds
AU - Yongzhu, Jin
AU - Hirose, Keiji
AU - Nakamura, Takashi
AU - Nishioka, Ryota
AU - Ueshige, Tetsuro
AU - Tobe, Yoshito
PY - 2006/10/6
Y1 - 2006/10/6
N2 - In order to develop a chiral stationary phase (CSP), which has even higher separation ability than the corresponding commercially available crown ether based CSP (OA-8000 having a pseudo-18-crown-6 ether with an OMe group as a selector), chemically bonded type CSP having a phenolic OH group on a crown ring was developed. Normal mobile phases with or without acid additive can be used with this OH type CSP in contrast to the conventional OMe type CSP which has a neutral chiral selector. Enantiomers of 25 out of 27 amino compounds, including 20 amino acids, 5 amino alcohols, and 2 lipophilic amines, were efficiently separated on a column with this CSP. Nine amino compounds out of 27 were separated with better separation factors than the corresponding OMe type CSP. It is noteworthy that the chromatography on this CSP exhibited excellent enantiomer-separations for amines and amino alcohols when triethyl amine was used as an additive in the mobile phase. Comparison of enantiomer separation ability on this OH type of CSP and on the OMe type of CSP and correlation between the enantioselectivity in chiral chromatography and that of the corresponding model compounds in solution imply that the chiral separation arose from chiral recognition in host guest interactions.
AB - In order to develop a chiral stationary phase (CSP), which has even higher separation ability than the corresponding commercially available crown ether based CSP (OA-8000 having a pseudo-18-crown-6 ether with an OMe group as a selector), chemically bonded type CSP having a phenolic OH group on a crown ring was developed. Normal mobile phases with or without acid additive can be used with this OH type CSP in contrast to the conventional OMe type CSP which has a neutral chiral selector. Enantiomers of 25 out of 27 amino compounds, including 20 amino acids, 5 amino alcohols, and 2 lipophilic amines, were efficiently separated on a column with this CSP. Nine amino compounds out of 27 were separated with better separation factors than the corresponding OMe type CSP. It is noteworthy that the chromatography on this CSP exhibited excellent enantiomer-separations for amines and amino alcohols when triethyl amine was used as an additive in the mobile phase. Comparison of enantiomer separation ability on this OH type of CSP and on the OMe type of CSP and correlation between the enantioselectivity in chiral chromatography and that of the corresponding model compounds in solution imply that the chiral separation arose from chiral recognition in host guest interactions.
KW - Amines
KW - Amino acids
KW - Amino alcohols
KW - Chemically bound type
KW - Chiral stationary phases
KW - Crown ethers
KW - Enantiomer separation
KW - Normal mobile phases
UR - http://www.scopus.com/inward/record.url?scp=33748551697&partnerID=8YFLogxK
U2 - 10.1016/j.chroma.2006.07.003
DO - 10.1016/j.chroma.2006.07.003
M3 - Article
C2 - 16872621
AN - SCOPUS:33748551697
VL - 1129
SP - 201
EP - 207
JO - Journal of Chromatography A
JF - Journal of Chromatography A
SN - 0021-9673
IS - 2
ER -